Are you at a life stage when you would like to reinvent your career, create a new career, semi-retire?

For myself, I would like to live out the second stage of my life with significance. So I decided to get some help. Whilst reading through some articles on, I chanced upon Gary Foreman’s( editor of Dollarstetcher) write-up about a book by Nancy Collamer called “Second Act Careers – 50+ Ways to Profit from Your Passions During Semi-Retirement”. The book is available in our local library. I decided to borrow out the book.

This article will include some insights I have gained after reading the book on creating ‘second-stage careers’.


The author, Nancy Collamer,  lives in Old Greenwich,  Connecticut, USA. She is a career consultant, speaker and author. She has a website


According to Collamer, many close to retirement or already retired do not want to spend their days engaging in leisure pursuits, every day or all day long.

At the book cover’s blurb, it mentions they “would like to continue working-whether to supplement their income or to stay mentally and physically active “.

It continues to argue for how the book  “Second-Act Careers”  shows how to “create a profitable and meaningful semi-retirement on your own terms and in your own way.”

Therefore, the book gives some suggestions on the kind of activities you might want to engage in during semi-retirement.


In Part 1, the author recommends ways of generating income as a semi-retiree,

In Part 2, she helps you figure out a matching career that will fit in with your interests, life experiences, talents and skills.


(1) Prepare Your Finances

Set aside 18 months of living expenses and also a smaller amount put aside each month for career reinvention. This will help your career or life makeover.

Preparing your finances also eases the transition stage for the amount of cash cough-up required during this time whilst your immediate family members get used to changes to your life and in their lives.

No harm too in putting a little extra aside as best of plans can be derailed and things sometimes never always go the way we plan them.

(2) Planning Your Life Backwards

There is an activity in the book that requires you to write your obituary.  I find that rather useful because it requires you to think about your end goal first.

It forces you to decide ahead those things you might still be ambivalent about – things like your beliefs (spirituality), whether to adhere to a religion as it will affect your funeral rites (if you want a funeral) and how you will like to be sent off. It does force one to  ‘piece together all the scattered parts of our lives’ to leave well.

Alternatively, it also allows us to plan ahead for necessary expenses or clarify information about send-offs in our local context.

I had to write a eulogy which enabled me to remember past, present or future achievements, work or accomplishments. I had to be honest about what I deeply care about. Whether it is family, friends, career or others, writing the speech allowed me to summarise my end of the journey with more clarity and I discovered I might have ‘wider’ goals I wanted to achieve and some legacies I might wish to be continued after my passing on.

(3) Adhere to  Goals Setting

Whilst revisiting my notes, I discovered the Goals Setting was already implemented in the follow-up activities which provides good suggestions on how or what to follow up.

You might have attended workshops that teach you how to set S.M.A.R.T. goals; this simply means your goals must be Specific, Measurable, Attainable, Realistic and Timely.

We know we must act on our goals. If yours doesn’t have a  ‘Time frame’ (Eg. By the time I am 55 years old, I will…) or you can’t ‘visualise’ your semi-retirement goal as something tangible ( that means you can’t experience it with one of the senses, that is, taste, touch, smell, sight or hearing), your ‘second-act career’ might not occur.


1) Invest in a career coach if you have no time to engage in self-study.

2) You will need at least 2 to 3 weekends to read through the sections you are keen to explore further, work through its several activities and thereafter revisit the notes again to let everything sink in to reformulate your retirement goals and actionable plan.

3) Be prepared for ‘Resistance’:  it may come from you (eg. Just seeing the word ‘Reinvention’ makes your heartbeat quicken) or the resistance could come from someone else.

4) Give it a chance to evolve: there are low-risk ways of trying it out like volunteering as mentioned in the book.

5) The useful range of world-wide web-based resources given in the book may not be applicable in Singapore so we would need to be creative:  visit our local community career fairs, exhibitions,  social media and search for or get by word-of-mouth relevant websites, all these whilst applying it to actionable steps outlined in the text.

6) Last but not least, keep an Open Mind and Be Mindful of Changes as it comes along.